‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic episode artwork

EPISODE · Feb 19, 2026 · 49 MIN

‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic

from Old School with Shilo Brooks · host The Free Press

One particular novel is all over the Epstein files: Vladimir Nabokov’s Lolita. Reportedly, this was the one and only book Jeffrey Epstein kept at his bedside table. He owned a first edition. It pops up in emails and in photos, released by the House Oversight Committee, that show young women with quotes from the book written on their bodies. Lolita is about a 38-year-old man who kidnaps and serially rapes a 12-year-old girl. The book is not only a literary masterpiece, but a fixture of American pop culture. The illicit relationship it depicts is often glamorized in film, music, and art.  Today, Rafaela Siewert interviews Shilo Brooks about Lolita–and about how a novel narrated by a homicidal pedophile rapist came to occupy such a prominent place in American life.  Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

One particular novel is all over the Epstein files: Vladimir Nabokov’s Lolita. Reportedly, this was the one and only book Jeffrey Epstein kept at his bedside table. He owned a first edition. It pops up in emails and in photos, released by the House Oversight Committee, that show young women with quotes from the book written on their bodies. Lolita is about a 38-year-old man who kidnaps and serially rapes a 12-year-old girl. The book is not only a literary masterpiece, but a fixture of American pop culture. The illicit relationship it depicts is often glamorized in film, music, and art.  Today, Rafaela Siewert interviews Shilo Brooks about Lolita–and about how a novel narrated by a homicidal pedophile rapist came to occupy such a prominent place in American life.  Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

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‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic

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This episode is 49 minutes long.

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This episode was published on February 19, 2026.

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One particular novel is all over the Epstein files: Vladimir Nabokov’s Lolita. Reportedly, this was the one and only book Jeffrey Epstein kept at his bedside table. He owned a first edition. It pops up in emails and in photos, released by the House...

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